A Novel Method for Functionalization of Non-Activated C-H Bond and Its Application to the Synthesis of Gibberellin A15: Chemical Studies on Diterpenoids. I
藥學雜誌 = Journal of the Pharmaceutical Society of Japan
巻
92
号
4
ページ
397 - 410
発行年
1972-01-01
ISSN
0031-6903
NCID
AN00284903
出版者
日本薬学会 = Pharmaceutical Society of Japan
抄録
On the assumption that non-activated C-H bond should be functionalized by the photolysis of some nitrones, the nitrone [24] derived from Enmein [1] in 14 steps was photodecomposed under various conditions, and the expected products [25 and 26] were obtained in a favorable yield. The structure of the compound [25] was determined unequivocally, and the possible mechanisms (d and e) (Fig. 4) were presumed. The compound [25] was then converted into gibberellin A15 in 6 steps. The route of [41]→[43]+[44] seems to be interesting, suggesting the biogenesis of gibberellin from kaurene.